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Metronidazole → Metronidazole Carbonate

HRID 533289
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 533289
ClC(Cl)([O:4][C:5](=[O:11])[O:6]C(Cl)(Cl)Cl)Cl.[CH3:13][C:14]1[N:18]([CH2:19][CH2:20][OH:21])[C:17]([N+:22]([O-:24])=[O:23])=[CH:16][N:15]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:13][C:14]1[N:18]([CH2:19][CH2:20][OH:21])[C:17]([N+:22]([O-:24])=[O:23])=[CH:16][N:15]=1.[C:5](=[O:4])([O-:11])[O-:6]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 4173MetronidazoleHCID 94429Triphosgene

Produkt 1

HCID 68777643Metronidazole CarbonateAusbeute 773,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

mPEG1 kDaOH (1.0 mmol, 1.0 g) and DMAP (2.4 mmol) were dissolved in anhydrous DCM (20 ml). Triphosgene (0.33 mmol, 99 mg) was added at room temperature. The solution was stirred at room temperature for 15 minutes. Metronidazole (1.1 mmol, 188 mg) was added and the reaction solution was stirred at room temperature for four hours. The solvent was evaporated at reduced pressure. The residue was extracted with DCM and 1N HCl solution (20 ml/20 ml) twice. The organic phases were combined and dried with anhydrous Na2SO4. The solid was filtered off and the solvent was evaporated. The residue was precipitated in ethyl ether/IPA (20 ml/10 ml). The compound 2e (590 mg, yield 50%) as solid was obtained by filtration. 1H NMR (CDCl3) δ 7.98 (s, 1H), 4.60 (t, 2H), 4.50 (t, 2H), 4.27 (t, 2H), 3.74-3.54 (m, 96H), 3.39 (s, 3H), 2.52 (s, 3H). MW 1308 [M+H]+.

Aufarbeitung

  1. stirringthe reaction solution was stirred at room temperature for four hours
  2. customThe solvent was evaporated at reduced pressure
  3. extractionThe residue was extracted with DCM and 1N HCl solution (20 ml/20 ml) twice
  4. dry with materialdried with anhydrous Na2SO4
  5. filtrationThe solid was filtered off
  6. customthe solvent was evaporated
  7. customThe residue was precipitated in ethyl ether/IPA (20 ml/10 ml)

Quellen und Nachweise

ORD-Eintrag
ord-91654e8a424b4f70a3da437e8efbedf0
Quelldatensatz
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08853247B2

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